Nematicidal activity of acetophenones and chalcones against Meloidogyne incognita and structure–activity considerations
2016
Caboni, Pierluigi | Aissani, Nadhem | Demurtas, Monica | Ntalli, Nikoletta | Onnis, Valentina
BACKGROUND: With the ultimate goal of identifying new compounds active against root‐knot nematodes, a set of 14 substituted chalcones were synthesised, starting from acetophenones. These chalcones and various acetophenones were tested in vitro against Meloidogyne incognita. RESULTS: The most potent acetophenones were 4‐nitroacetophenone and 4‐iodoacetophenone, with EC₅₀ /₂₄ ₕ values of 12 ± 5 and 15 ± 4 mg L⁻¹ respectively, somewhat weaker than that of the chemical control fosthiazate in our previous experiments (EC₅₀ /₂₄ ₕ 0.4 ± 0.3 mg L⁻¹). When we converted the acetophenones to chalcones, the nematicidal activity differed, based on their substitution pattern. The condensation of 4‐nitroacetophenone with 2,4,6‐trihydroxybenzaldehyde to give the corresponding chalcone (E)‐1‐(4‐nitrophenyl)‐3‐(2,4,6‐trihydroxyphenyl)prop‐2‐en‐1‐one led to a slight reduction in activity (EC₅₀ /₂₄ ₕ value 25 ± 17 mg L⁻¹). Moreover, (E)‐3‐(2‐hydroxy‐5‐iodophenyl)‐1‐(4‐methoxyphenyl)prop‐2‐en‐1‐one showed better activity (EC₅₀ /₂₄ ₕ value 26 ± 15 mg L⁻¹) than 4‐methoxyacetophenone (EC₅₀ /₂₄ ₕ value 43 ± 10 mg L⁻¹). CONCLUSIONS: Acetophenones and chalcones may represent good leads in the discovery of new nematicidal compounds and may have potential use in crop management as active ingredients. © 2015 Society of Chemical Industry
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